Benzene → HCID 22867072, 화합물

HRID 1682707노트

반응식

HRID 1682707 반응식
[NH2:1][CH2:2][C@H:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[OH:4].O=[C:12]([CH3:24])[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][OH:23])=[CH:17][CH:16]=1.C1C=CC=CC=1.C([BH3-])#N.[Na+]>O.CO>[OH:23][CH2:22][CH2:21][C:18]1[CH:19]=[CH:20][C:15]([O:14][CH2:13][CH:12]([NH:1][CH2:2][C@H:3]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[OH:4])[CH3:24])=[CH:16][CH:17]=1

참가 물질

7

반응물 4

HCID 241BenzeneHCID 643217(1S)-2-amino-1-phenylethan-1-olHCID 5003444Sodium cyanoborohydrideHCID 218321652-[4-(2-Oxopropoxy)phenyl]ethanol

생성물 1

HCID 22867072HCID 22867072, 화합물수율 16.5%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

A procedure similar to that described in Example 3 was repeated, except that 1.4 g of 2-amino-1(S)-phenylethanol (prepared as described in Preparation 16), 2.4 g of 2-[4-(2-oxopropoxy)phenyl]ethanol (prepared as described in Preparation 7), 100 ml of benzene, 100 ml of absolute methanol and 0.95 g of sodium cyanoborohydride were used and that, after the reaction, the reaction mixture was diluted with water and extracted with ethyl acetate. The extract was then concentrated by evaporation under reduced pressure, and the concentrate was purified by column chromatography through silica gel, using a 30:1 by volume mixture of ethyl acetate and ethanol as the eluent. 0.53 g of the title compound was obtained as crystals, melting at 93°-96° C. (after recrystallization from ethyl acetate).

후처리

  1. customthat, after the reaction
  2. extractionextracted with ethyl acetate
  3. concentrationThe extract was then concentrated by evaporation under reduced pressure
  4. customthe concentrate was purified by column chromatography through silica gel
  5. additionby volume mixture of ethyl acetate and ethanol as the eluent

출처 및 근거

ORD 기록
ord-3e27a23634fb41128ce92e29fa75d767
출처 데이터셋
uspto-grants-1997_06
특허 번호
US05635534

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